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gamma-Terpinene (FDB015968)

Record Information
Version1.0
Creation date2010-04-08 22:12:09 UTC
Update date2020-09-17 15:31:31 UTC
Primary IDFDB015968
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namegamma-Terpinene
Descriptiongamma-Terpinene belongs to the class of organic compounds known as menthane monoterpenoids. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Menthanes are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and an isopropyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. gamma-Terpinene is one of 4 isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton.
CAS Number99-85-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP4.36ALOGPS
logP3.16ChemAxon
logS-2.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.55 m³·mol⁻¹ChemAxon
Polarizability17.61 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16
IUPAC name1-methyl-4-(propan-2-yl)cyclohexa-1,4-diene
InChI IdentifierInChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3
InChI KeyYKFLAYDHMOASIY-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1=CCC(C)=CC1
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
Classification
Description Belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassBranched unsaturated hydrocarbons
Direct ParentBranched unsaturated hydrocarbons
Alternative Parents
Substituents
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Olefin
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting Point-10 oC
Boiling PointBp 183°DFC
Experimental Water Solubility0.00868 mg/mL at 22 oCLI,J & PERDUE,EM (1995)
Experimental logP4.50LI,J & PERDUE,EM (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9300000000-97923633c0b05f03274f2014-09-20View Spectrum
GC-MSgamma-Terpinene, non-derivatized, GC-MS Spectrumsplash10-0006-9200000000-b05d52aa0731550051f6Spectrum
GC-MSgamma-Terpinene, non-derivatized, GC-MS Spectrumsplash10-0006-9400000000-a5cb265912cd3b36ec3fSpectrum
GC-MSgamma-Terpinene, non-derivatized, GC-MS Spectrumsplash10-0006-9500000000-2b0e829aa7638afa325eSpectrum
GC-MSgamma-Terpinene, non-derivatized, GC-MS Spectrumsplash10-0006-9200000000-b05d52aa0731550051f6Spectrum
GC-MSgamma-Terpinene, non-derivatized, GC-MS Spectrumsplash10-0006-9400000000-a5cb265912cd3b36ec3fSpectrum
GC-MSgamma-Terpinene, non-derivatized, GC-MS Spectrumsplash10-0006-9500000000-2b0e829aa7638afa325eSpectrum
GC-MSgamma-Terpinene, non-derivatized, GC-MS Spectrumsplash10-0006-9200000000-85beacebb887bcf22446Spectrum
Predicted GC-MSgamma-Terpinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9300000000-78ed493eae24d7cd7247Spectrum
Predicted GC-MSgamma-Terpinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0019-8900000000-4f8f18604be188d356c82012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-015c-9000000000-7cd3ebd6c5315af11ec52012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002f-9000000000-796d72dfa199c02320d22012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9200000000-ddf6ab2c599f6a3a0e042012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0006-9400000000-701e197e734bd825ea092012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0006-9500000000-156890c59245ff11b54d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-Q-TOF/MS 25V, negativesplash10-000i-0900000000-98cfc7dd6d4b6ccbba0b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-Q-TOF/MS 30V, negativesplash10-0019-2900000000-898e1880d94396f2ba762020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-7132f17a85333e7849562015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9700000000-f4bee8ac3721685bb6062015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-dbeffc46ec6acbacb6ef2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-545d284bbb3189d5973d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-838b737755ef4340d8a22015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-6900000000-6351b5255caae6105b152015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000m-9500000000-380389192d752a66b55d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0036-9000000000-6d366a78065dacee15ff2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-ce8dcdbeb3aaa0e182052021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9600000000-571ac1102d9ec6dc48522021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 50.32 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Spectrum
ChemSpider ID7181
ChEMBL IDCHEMBL449693
KEGG Compound IDC09900
Pubchem Compound ID7461
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05806
CRC / DFC (Dictionary of Food Compounds) IDKLQ43-T:KLQ43-T
EAFUS ID3606
Dr. Duke IDGAMMA-TERPINENE
BIGG IDNot Available
KNApSAcK IDC00003061
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID99-85-4
GoodScent IDrw1017031
SuperScent IDNot Available
Wikipedia IDTerpinene
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
acaricide22153 A substance used to destroy pests of the subclass Acari (mites and ticks).DUKE
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti acetylcholinesterase38462 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.DUKE
anti feedantDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
gasoline
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
turpentine
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
lime
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
terpene
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lemon
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tropical
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.